GW842166X

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Search structure


Synonyms	GW 842166 GW 842166X GW-842166 GW842166 Gw-842,166x Gw842166x
Status
Molecule Category	UNKNOWN
UNII	VL1I6P2DZ8
EPA CompTox	DTXSID60216786


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	TWQYWUXBZHPIIV-UHFFFAOYSA-N
Smiles	O=C(NCC1CCOCC1)c1cnc(Nc2ccc(Cl)cc2Cl)nc1C(F)(F)F
InChI	InChI=1S/C18H17Cl2F3N4O2/c19-11-1-2-14(13(20)7-11)26-17-25-9-12(15(27-17)18(21,22)23)16(28)24-8-10-3-5-29-6-4-10/h1-2,7,9-10H,3-6,8H2,(H,24,28)(H,25,26,27)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C18H17Cl2F3N4O2
Molecular Weight	449.26
AlogP	4.7
Hydrogen Bond Acceptor	5.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	5.0
Polar Surface Area	76.14
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	29.0

Bioactivity

Mechanism of Action	Action	Reference
Cannabinoid CB2 receptor agonist	AGONIST	PubMed


Protein: Cannabinoid CB2 receptor Description: Cannabinoid receptor 2 Organism : Homo sapiens P34972 ENSG00000188822

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Cannabinoid receptor	50-437	-	-	-	12

Assay Description	Organism	Bioactivity	Reference
Agonist activity at human recombinant CB2 receptor expressed in Saccharomyces cerevisiae cells	Homo sapiens	63.0 nM
Agonist activity at rat CB2 receptor	Rattus norvegicus	91.0 nM
Agonist activity at human CB2 receptor expressed in CHO cells assessed as inhibition of forskolin-stimulated cAMP level	Homo sapiens	63.0 nM
Agonist activity at CB2 receptor	None	50.0 nM
Displacement of [3H]CP-55940 from human recombinant CB2 receptor	Homo sapiens	50.0 nM
Agonist activity at human CB2 receptor expressed in CHO cells assessed as inhibition of forskolin-induced cAMP release	Homo sapiens	350.0 nM
Agonist activity at human recombinant cannabinoid CB2 receptor expressed in MMY23 Saccharomyces cerevisiae assessed as degradation of FDGlu to fluorescein after 24 hrs by spectrofluorimetry	Homo sapiens	63.0 nM
Agonist activity at CB2 receptor (unknown origin) expressed in CHO cells by calcium mobilization assay	Homo sapiens	431.0 nM
Agonist activity at CB2R (unknown origin) CHO cells stably expressing Galpha16 assessed as increase in intracellular calcium level by microplate reader based assay	Homo sapiens	437.0 nM
Agonist activity at CB2 receptor (unknown origin) expressed in CHO cells co-expressing G-alpha16 incubated for 24 hrs by fluo-4 AM dye based whole-cell calcium mobilization assay	Homo sapiens	342.8 nM
Antagonist activity at CB1 receptor (unknown origin) expressed in CHO cells assessed as inhibition of CP55940-induced calcium mobilization at 10 uM preincubated for 10 mins followed by CP55940-induction by fluo-4 AM dye-based fluorescence assay relative to SR141716A	Homo sapiens	11.78 %
Agonist activity at CB2 receptor (unknown origin) expressed in CHO cells assessed as induction of calcium mobilization by fluo-4 AM dye-based fluorescence assay	Homo sapiens	342.8 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	2.29 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	9.73 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	1.458 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.04 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.14 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.14 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.04 %

Cross References

Resources	Reference
ChEMBL	CHEMBL225411
DrugBank	DB11903
FDA SRS	VL1I6P2DZ8
SureChEMBL	SCHEMBL3015040
ZINC	ZINC000003947932

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).